246 PRACTICAL ORGANIC CHEMISTRY
action of bromine and caustic potash, phthalaminic acid is first
formed, which then yields the ammo-acid,
C6H4< >NII + HoO = CBH4<
NrCK ~ XX)OH
C6H / " + Bro = C6H4< + HBr.
QIV = CflH/ + IIBr.
C6H4<; + HoO = CJI4< " +• CO.,.
XCOOII " \COOH
The primary amines may also be obtained by the following
1. Action of alcoholic ammonia on the alkyl iodides jincl
C2HSI + NIT8 = C2H5NH2 + HI. (Hofmann.)
Secondary and tertiary amines are also formed (see p. 156),
C2HSONO2 + NH3 = CoH5NIIo + IINO«. (Wallach.)
2. Reduction of the following classes of compounds :
C2H5NO2 + sH2 = C2H,NH2 + aH2O. (V. Meyer.)
C2HaCN + 2lI3 = CoH.CHoNIio. (Mendius.)
CH3.CH:NOH + 2H2 = CH3.CH2.N.ri2 + H2O. (Goldschmidt.)
CH8.CH:N.NHCGH5 + 2H3 = CH3.CH2.NH2 -f CflII5.NIIo. (Tafel.)
3. Hydrolysis of the isocyanides with cone. HC1, which occurs
in two steps :
C2H5NC + HoO = C2HBNII.COH
C2H5NH.COH + HoO = C2H5NH2 + HCO.OIT.
Th- three classes of aliphatic amines (primary, secondary, and
tertiary) may be disting'uished by their behaviour with nitrous